6-Chloropyrimidin-4(3H)-one Chemical Properties

Melting point:

194 °C

Boiling point:

199.4±50.0 °C(Predicted)

Density 

1.55±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO, Water

form 

Solid

pka

6.92±0.40(Predicted)

color 

Off-White to Pale Yellowish

CAS DataBase Reference

4765-77-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-37/38-22

Safety Statements 

22-26-36/37/39-39

HS Code 

2933599590

6-Chloropyrimidin-4(3H)-one Usage And Synthesis

Chemical Properties

Off-White to Pale Yellowish Solid

Uses

4-Chloro-6-hydroxypyrimidine (cas# 4765-77-9) is a compound useful in organic synthesis.

Definition

ChEBI: 6-Chloro-4-pyrimidinol is an organohalogen compound and a member of pyrimidines.

Synthesis

The general procedure for the synthesis of 6-chloropyrimidin-4(3H)-ones from 4,6-dichloropyrimidines is as follows: Intermediate 1: Synthesis of 6-chloro-3H-pyrimidin-4-one 4,6-Dichloropyrimidine (Aldrich; 10.00 g, 67.1 mmol), concentrated hydrochloric acid (50 mL), water (50 mL), and dioxane (50 mL) were mixed and heated at 70 °C for 6 h, and subsequently cooled to room temperature to obtain a pink solution. The solvent was removed by evaporation under reduced pressure (using a vacuum pump) to obtain a pink solid. Ethanol (50 mL) was added to the solid and the mixture was heated until the solid was completely dissolved. The solution was cooled slowly in a warm water bath at about 50°C. After standing overnight, it was filtered to obtain an off-white solid, 6-chloro-3H-pyrimidin-4-one (5.02 g, 57% yield), with a melting point of 193-194°C (literature value: 192-193°C, see DJ Brown and JS Harper, J. Chem. Soc. 1961, 1298-1303). 1H NMR (d6-DMSO) data: δ 6.50 (s, 1H), 8.19 (s, 1H), 13.00 (br s, 1H).

References

[1] Journal of the Chinese Chemical Society, 2013, vol. 60, # 1, p. 27 - 34
[2] Patent: US2009/149466, 2009, A1
[3] Patent: WO2017/59080, 2017, A1. Location in patent: Page/Page column 288; 289

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